立体化学定义的alpha-sulfonamidoorganostannanes的静态合
Kevin W Kells1, J Michael Chong
1Guelph-Waterloo Centre for Graduate Work in Chemistry and Biochemistry, Department of Chemistry, University of Waterloo, Waterloo, Ontario, Canada N2L 3G1.
Journal of the American Chemical Society
|December 2, 2004
概括
这项研究引入了一种新方法,用于合成使用tributylstannylmetallics和arylaldehydes的α-sulfonamidostannanes. 由此产生的化合物经历静态合,显示出高的二聚体选择性和配置反转.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 有机金属化学 有机金属化学
背景情况:
- 硫胺是药物化学中的关键功能组.
- 静态合是一种重要的碳-碳键形成反应.
- 奇拉化合物的立体选择性合成仍然是一个重大挑战.
研究的目的:
- 开发一种新型的立体选择性途径,以获得α-硫胺.
- 探索这些中间体在催化交叉合反应中的实用性.
- 为了研究合成转换的立体化学结果.
主要方法:
- 在 (R) - tert-butanesulfonimine 和 arylaldehydes 的衍生物中添加微基基金属.
- 使用m-CPBA的中间α-sulfinamidostannanes的氧化.
- 帕拉/铜催化Stille型合剂与化,使用tris(2,4,6-trimethoxyphenyl) 素连接物.
主要成果:
- 在alpha-sulfinamidostannanes的形成中获得的高二选择性 (>98%de).
- 通过氧化成功合成alpha-sulfonamidostannanes.通过氧化成功合成alpha-sulfonamidostannanes.
- 有效的Stille合器产生所需的产品,在基碳的配置反转.
结论:
- 已经建立了一种强大的立体选择方法来合成α-硫胺.
- 开发出来的中间体对静态合反应有价值.
- 反应以可预测的立体化学逆转在化物位置进行.
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